Vacation rentals with outdoor seating in Wintergreen Resort

We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!

Three couples wanted a central meeting place to spend some quality time catching up with each other. It was just the perfect place! We had a nice time talking in the hot tub, around the fire on the cozy porch, and in the exquisite pool. The goats added a nice touch to this country setting. The kitchen had all the cooking supplies we needed and more. We did a good bit of eating onsite so that was appreciated. We unfortunately didn’t use the pingpong table or other games but they were there to enjoy. There were plenty of towels and the new washer and dryer were great. It’s a great location to experience the many local wineries. Bobbi and Keith were excellent hosts, friendly and gave great suggestions of things to do. Everything about our stay was wonderful. We hope to return soon!

Great house layout with a beautiful porch and lots of parking. The host is very responsive and helpful. It’s a little off the beaten path but close to lots of breweries and wineries. Would absolutely stay here again.

I was looking for a quiet place in the middle of the nature for our 10 years of marriage anniversary and I think we found the best one. Charlotte was so kind and helpful, she helped me surprised my wife with such a beautiful decoration. We were so impressed. My kids were so happy 😊😊 to see something different. If you’re looking for something really peaceful, nice, looking at the beautiful nature in the mountains, you are definitely at the right place. Thank you Charlotte for making our stay so special.😊😊😊😊 It was a really good experience and we definitely have to go back….

⭐️⭐️⭐️⭐️⭐️ Beautiful Stay with Local Gems & a Disc Golf Bonus This Airbnb was a total gem! The space is beautifully designed—clean, cozy, and full of thoughtful touches that made it feel like home. Amy is warm, responsive, and provided fantastic local suggestions that really elevated our trip. Highlights included the community center with Trager’s coffee (a perfect morning stop), a fun local thrift shop, and a charming rock shop that felt like a hidden treasure. The neighborhood had such a welcoming, creative vibe—we loved exploring it all. And for the disc golfers out there: Walnut Hill Park is about 30 minutes away and absolutely worth the trip. It was every bit as amazing as we hoped—great course, beautiful setting, must go play!! We will be back!!! This place is a perfect mix of comfort, character, and local flavor!

Great place, very cozy yet plenty of space. Well stocked and well outfitted. Looking forward to going back.

Very clean and affordable. The hot tub was sooooooo nice. I can't recommend it enough.

What a lovely home with stunning views. Very convenient location. Close to everything, Charlottesville, Afton, the Crozet railroad tunnel, mountains etc. The house itself is super cool. Open modern design equiped with everything. The sauna is wonderful! The Our hosts thought of everything! We often commented on the little things we came across that made an impression. Justin was very responsive and made every effort to make sure our accommodations were perfect. Thank you for the wonderful espresso Justin! How nice to wake up in the morning to the gorgeous views while sipping coffee shop quality espresso. We hope to come back every year.

Ed and Camille were amazing, they have a sweet apartment with a great Jacuzzi and pool. We were in town for a wedding and were blessed that Ed’s spot was open as it was only 15 minutes from the wedding venue. The apt was clean and everything was working, the kitchen was spotless as well. Ed and Camille were great, very communicative and nice people.

Deidre and Scotty’s place is such a delight! I only stayed for one night but it was so comfortable and well designed that I wished I had time to stay longer. The space was so easy to relax in and if it weren’t stormy out I so would have been hanging out on the beautiful porch. I will definitely try to come back!

Staunton is a beautiful little town, very pedestrian with nice cafes and restaurants. Staying at this wonderful 'hideaway' flat was the perfect base from which to explore Staunton. Inside the flat we loved the dart board and sauna, very unique! Decoration was top notch and the bed was a great night's sleep. Would definitely stay here again.

Ellen’s apartment is a fantastic place to stay for a visit to Staunton. Be aware there are 52 stairs (per Ellen herself) to get up to the apartment, but there was an elevator to help with luggage for the first two floors. It kept us in shape after all the eating we did, but may be a consideration for folks with more limited mobility. The apartment is spacious with lovely decor and great views, even from the (huge) bathroom. The outdoor deck shouldn’t be missed.

Beautifully decorated and extremely clean! Had everything we could have possibly wanted and the location was perfect for visiting wineries and breweries! We would definitely stay here again on our next visit to the area!

Great getaway! Peaceful neighborhood literally a 5 minute walk through a park and over the historic railroad bridge to the shops and restaurants in downtown Staunton. Kitchen was well stocked and the place is decorated with cleaver and eclectic decor. Beautiful historic building with updated/newly renovated interior amenities. Shea was helpful, very accommodating and responsive. Can’t say enough about how nice our stay was - and we’ll definitely be back! Oh yeah - hiking in the mountains was one of our reasons for coming to the area - and the entrance to Skyline Drive is like 15 minutes away. It was the perfect spot for our birthday get away!

It’s a beautiful space. We booked the airbnb last minute as we were in town and stayed the night. It’s in a convent location walking distance to the farmers market that we enjoy. Staunton is a beautiful town.

Beautiful scenery. Lovely roads to walk up and down. We were too cold for the pool, but got plenty of use out of the fire pit. We enjoyed ourselves. There were a couple kinks along the way, but the host always responded when we reached out and addressed our concerns right away.

Laleh is a great and perfect host. I have stayed with her numerous times and I have enjoyed her space, her continued communication and her quickness to address any number of questions. Enjoy your stay with her.

This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!

We loved our stay. It was exactly what we were looking for. The house is wonderful and very comfortable. Our kids loved the house, the area around it, and the hiking.

Nice home, in an ideal location. Great communication and quick to respond as needed. Recommend the home and location!

This was the perfect spot for our trip. A friend of mine and I brought our teenage sons for a quick weekend snowboarding trip, and needed somewhere with three sleeping areas. The loft had 2 beds and a fully bath which was exactly what we needed for the boys. It was super convenient to everything with a shuttle stop right out front. Plenty of parking, great amenities, clean, and easy to find! Also very cozy! We’ll definitely return!

Absolutely a gem!! Loved the super clean, comfortable (especially the huge soft sofa!) space. Kitchen had all the basics we needed, and everything worked as expected. Was the perfect location for our home base as we section-hiked the Appalachian Trail for a week. Would definitely stay again!

We had a wonderful time while staying at this condo. There kitchen had plenty of pots and pans, the deck was relaxing, the bed we slept in downstairs was extremely comfortable. When Emile found out we were going to get in late, he had someone turn on the outside light. So nice because it would have been harder to get into the lockbox. So happy we stayed here for our getaway from the city.

Amazing view and condo! We loved our stay!